Synthesis of 2,3,8,9,14,15-Hexamethyl-5,6,11,12,17,18-Hexadehydrotribenzo Annulene and the Reductive-Hydration of Ortho-Nitrophenylacetylenes
Date of Graduation
Master of Science in Chemistry
In order to develop a new procedure for the self-assembly of nanochannels using electron donor-acceptor complexation an electron rich annulene was synthesized. Thus through a multi-step procedure the molecule 2,3,8,9,14,15-hexamethyl-5,6,11,12,17,18-hexadehydrotribenzoannulene was synthesized. During this synthesis a novel reductive-hydration reaction was discovered and investigated. The investigation revealed that reduction of ortho-nitro-phenylacetylenes with common reducing agents resulted in the hydration of the acetylene moiety to a methyl-ketone concomitant with reduction of the nitro group to the corresponding amine.
© Laura Jeffries
Jeffries, Laura, "Synthesis of 2,3,8,9,14,15-Hexamethyl-5,6,11,12,17,18-Hexadehydrotribenzo Annulene and the Reductive-Hydration of Ortho-Nitrophenylacetylenes" (2001). MSU Graduate Theses. 2399.